3-O-benzyl-5-O-tert-butyldiphenylsilyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate)

Base Information

Chemical Name:3-O-benzyl-5-O-tert-butyldiphenylsilyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate)
CAS No.:765274-04-2
Molecular Formula:C₄₀H₄₆O₆Si
Molecular Weight:650.887
Hs Code.:

Synonyms:3-O-benzyl-5-O-tert-butyldiphenylsilyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate)

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Chemical Property of 3-O-benzyl-5-O-tert-butyldiphenylsilyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate)

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Technology Process of 3-O-benzyl-5-O-tert-butyldiphenylsilyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate)

There total 6 articles about 3-O-benzyl-5-O-tert-butyldiphenylsilyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

: 100-39-0
benzyl bromide

: 1001894-68-3
(3aS,5R,6R,6aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-pent-4-enyloxy-2-phenyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

: 765274-04-2
3-O-benzyl-5-O-tert-butyldiphenylsilyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate)

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;
DOI:10.1021/ol0490680

Reference yield:

: 821-09-0
n-Pent-4-enyl alcohol

: 765274-04-2
3-O-benzyl-5-O-tert-butyldiphenylsilyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate)

Guidance literature:: Multi-step reaction with 4 steps

1: 70 percent / 2,6-lutidine; tetra-n-butylammonium iodide / CH₂Cl₂ / 72 h / Heating

2: 75 percent / NaOMe / methanol; CH₂Cl₂ / 2 h / 20 °C

3: 62 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

4: 80 percent / NaH / dimethylformamide / 1 h / 0 °C

With 2,6-dimethylpyridine; dmap; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0490680

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 765274-04-2
3-O-benzyl-5-O-tert-butyldiphenylsilyl-β-D-arabinofuranose 1,2-(pent-4-enyl orthobenzoate)

Guidance literature:: Multi-step reaction with 2 steps

1: 62 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

2: 80 percent / NaH / dimethylformamide / 1 h / 0 °C

With dmap; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0490680